The conduct of detectives who convinced a learning disabled 16-year-old boy to confess to a rape and murder in the "Making a Murderer" case "made my skin crawl," a federal appeals court judge in Chicago said Tuesday.

Dassey's mother, Barbara Dassey, and other relatives traveled from Manitowoc County to Chicago to hear oral arguments in the latest attempts to spring Dassey from a life sentence behind bars. He was convicted alongside his uncle StevenAvery after giving a video confession that his lawyers say was coerced by cops who took advantage of his severely limited intelligence and high suggestibility. Brendan also was let down by his original attorney, who later admitted he had been on the side of victim Teresa Halbach.

After the Netflix documentary gave the younger Dassey's appeal fresh impetus, a lower federal court last year ruled that he should be retried within 90 days or freed. A three-judge panel of 7th Circuit judges in June upheld that ruling 2-1, but Wisconsin asked for the case to be reconsidered by all seven judges.

And a series of sharp and at times sarcastic comments by Wood, including the comment that "the detectives made my skin crawl with this lulling behavior that was so dishonest, so dishonest, with such a vulnerable person," strongly hinted that she is likely also to side with Dassey.

But Judge Diane Sykes — mentioned by President Donald Trump as a possible U.S. Supreme Court justice — saved her fire for Dassey's attorney Laura Nirinder, accusing her of wanting the court to "create new law" by finding that detectives' promise to the simple-minded Dassey that "the truth will set you free" constituted a promise he would be released, given Dassey's IQ of just 81 and his literal-mindedness.

Along with Judge David Hamilton, who voted against freeing Dassey in June, and Judge Michael Kanne, who also saved his toughest questions for Nirinder, that would make three judges on each side.

While predicting how judges will rule based on oral arguments can be a mug's game, it could be that the deciding vote will be Judge FrankEasterbrook's. Often the fiercest inquisitor on the bench, Easterbrook was the only judge not to speak during Tuesday's hearing.